#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/25/4022511.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4022511
loop_
_publ_author_name
'Evelyne Dietrich'
'William D. Lubell'
_publ_contact_author
;
    Dr William D. Lubell
    Departement de Chimie
    Universite de Montreal
    C.P. 6128, Succ. Centre-ville
    Montreal, Quebec
    Canada H3C 3J7
;
_publ_contact_author_email       lubell@chimie.umontreal.ca
_publ_contact_author_fax         '514 343 7586'
_publ_contact_author_phone       '514 343 7339'
_publ_section_title
;
 Efficient Synthesis of Enantiopure Pyrrolizidinone Amino Acid
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6988
_journal_page_last               6996
_journal_paper_doi               10.1021/jo034739d
_journal_volume                  68
_journal_year                    2003
_chemical_compound_source        'synthesized by the authors, see text'
_chemical_formula_moiety         'C14 H22 N2 O5'
_chemical_formula_sum            'C14 H22 N2 O5'
_chemical_formula_weight         298.336
_chemical_name_common
;
(3S,5R,8S)-methyl 3-[N-(Boc)]
amino-1-azabicyclo[3.3.0]octan-2-one 8-carboxylate
;
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'SHELXL96 (Sheldrick, 1996)'
_cell_angle_alpha                90.00
_cell_angle_beta                 124.96(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.601(13)
_cell_length_b                   6.823(2)
_cell_length_c                   15.622(7)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.00
_cell_measurement_theta_min      20.00
_cell_volume                     1624.9(14)
_computing_cell_refinement       'CAD-4 software (Enraf-Nonius, 1989)'
_computing_data_collection       'CAD-4 software (Enraf-Nonius, 1989)'
_computing_data_reduction        'NRC-2, NRC-2A (Ahmed et al, 1973)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'SHELXL96 (Sheldrick, 1996)'
_computing_structure_refinement  'SHELXL96 (Sheldrick, 1996)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device_type  'Nonius CAD-4'
_diffrn_measurement_method       'ω scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus xray tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54056
_diffrn_reflns_av_R_equivalents  0.037
_diffrn_reflns_av_sigmaI/netI    0.0405
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            31265
_diffrn_reflns_theta_max         69.77
_diffrn_reflns_theta_min         3.45
_diffrn_standards_decay_%        4.6
_diffrn_standards_interval_time  60
_diffrn_standards_number         5
_exptl_absorpt_coefficient_mu    0.773
_exptl_absorpt_correction_T_max  0.9102
_exptl_absorpt_correction_T_min  0.7739
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'ABSORP in NRCVAX (Gabe et al, 1989)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.2195
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       block
_exptl_crystal_F_000             640.0
_exptl_crystal_size_max          0.57
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.098
_refine_diff_density_min         -0.118
_refine_diff_density_rms         0.026
_refine_ls_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   0.3(3)
_refine_ls_extinction_coef       0.0038(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL96 (Sheldrick, 1996)'
_refine_ls_goodness_of_fit_all   0.847
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         3051
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.847
_refine_ls_restrained_S_obs      1.007
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0472
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0671P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1134
_refine_ls_wR_factor_ref         0.1091
_reflns_number_gt                2052
_reflns_number_total             3051
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            jo034739dsi20030530_034925.cif
_cod_data_source_block           lube24
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               4022511
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N 0.11501(13) 0.1522(3) -0.11707(17) 0.0605(5) Uani 1 d .
C2 C 0.15696(15) 0.2009(4) -0.0155(2) 0.0601(6) Uani 1 d .
O2 O 0.16220(13) 0.3650(3) 0.01782(17) 0.0781(6) Uani 1 d .
C3 C 0.19275(16) 0.0140(4) 0.0474(2) 0.0640(7) Uani 1 d .
H3 H 0.2524 -0.0078 0.0666 0.077 Uiso 1 calc R
C4 C 0.1323(2) -0.1410(4) -0.0309(2) 0.0749(8) Uani 1 d .
H4A H 0.0797 -0.1555 -0.0323 0.090 Uiso 1 calc R
H4B H 0.1616 -0.2668 -0.0149 0.090 Uiso 1 calc R
C5 C 0.11071(19) -0.0603(4) -0.1338(2) 0.0699(7) Uani 1 d .
H5 H 0.1558 -0.1004 -0.1441 0.084 Uiso 1 calc R
C6 C 0.0201(2) -0.0893(5) -0.2343(2) 0.0829(9) Uani 1 d .
H6A H -0.0232 -0.1153 -0.2198 0.100 Uiso 1 calc R
H6B H 0.0200 -0.1963 -0.2752 0.100 Uiso 1 calc R
C7 C 0.00258(19) 0.1060(5) -0.2903(2) 0.0826(9) Uani 1 d .
H7A H -0.0599 0.1272 -0.3401 0.099 Uiso 1 calc R
H7B H 0.0306 0.1104 -0.3269 0.099 Uiso 1 calc R
C8 C 0.04194(16) 0.2593(4) -0.2037(2) 0.0652(7) Uani 1 d .
H8 H 0.0615 0.3759 -0.2215 0.078 Uiso 1 calc R
N10 N 0.19509(13) 0.0261(4) 0.14114(17) 0.0697(6) Uani 1 d .
H10 H 0.1467 0.0197 0.1363 0.084 Uiso 1 calc R
C11 C 0.27060(16) 0.0471(5) 0.2356(2) 0.0706(7) Uani 1 d .
O11 O 0.34311(11) 0.0308(4) 0.25471(16) 0.0982(7) Uani 1 d .
O12 O 0.25294(11) 0.0874(3) 0.30624(14) 0.0786(6) Uani 1 d .
C12 C 0.3242(2) 0.1276(6) 0.4149(2) 0.0909(10) Uani 1 d .
C13 C 0.3791(3) -0.0540(8) 0.4653(3) 0.1304(16) Uani 1 d .
H13A H 0.3413 -0.1638 0.4505 0.196 Uiso 1 calc R
H13B H 0.4176 -0.0350 0.5395 0.196 Uiso 1 calc R
H13C H 0.4131 -0.0787 0.4380 0.196 Uiso 1 calc R
C14 C 0.2738(3) 0.1764(9) 0.4618(3) 0.1286(16) Uani 1 d .
H14A H 0.2397 0.2930 0.4297 0.193 Uiso 1 calc R
H14B H 0.3143 0.1973 0.5356 0.193 Uiso 1 calc R
H14C H 0.2354 0.0696 0.4497 0.193 Uiso 1 calc R
C15 C 0.3764(3) 0.3032(8) 0.4213(3) 0.1280(15) Uani 1 d .
H15A H 0.4084 0.2704 0.3923 0.192 Uiso 1 calc R
H15B H 0.4167 0.3410 0.4931 0.192 Uiso 1 calc R
H15C H 0.3372 0.4100 0.3827 0.192 Uiso 1 calc R
C16 C -0.02325(16) 0.3109(4) -0.1774(2) 0.0674(7) Uani 1 d .
O16 O -0.03850(12) 0.2086(3) -0.12774(18) 0.0861(6) Uani 1 d .
O17 O -0.06257(13) 0.4805(3) -0.21919(18) 0.0891(7) Uani 1 d .
C17 C -0.1234(2) 0.5452(6) -0.1947(3) 0.1130(12) Uani 1 d .
H17A H -0.1758 0.4671 -0.2328 0.170 Uiso 1 calc R
H17B H -0.1381 0.6803 -0.2139 0.170 Uiso 1 calc R
H17C H -0.0966 0.5306 -0.1211 0.170 Uiso 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C2 N1 C8 125.1(2) y
C2 N1 C5 112.9(2) y
C8 N1 C5 113.9(2) y
O2 C2 N1 125.5(3) y
O2 C2 C3 127.0(3) y
N1 C2 C3 107.4(2) y
N10 C3 C2 110.9(2) y
N10 C3 C4 115.8(2) y
C2 C3 C4 102.6(2) y
N10 C3 H3 109.1 ?
C2 C3 H3 109.1 ?
C4 C3 H3 109.1 ?
C3 C4 C5 103.0(2) y
C3 C4 H4A 111.2 ?
C5 C4 H4A 111.2 ?
C3 C4 H4B 111.2 ?
C5 C4 H4B 111.2 ?
H4A C4 H4B 109.1 ?
N1 C5 C4 102.5(2) y
N1 C5 C6 103.1(2) y
C4 C5 C6 120.6(3) y
N1 C5 H5 109.9 ?
C4 C5 H5 109.9 ?
C6 C5 H5 109.9 ?
C5 C6 C7 103.0(3) y
C5 C6 H6A 111.2 ?
C7 C6 H6A 111.2 ?
C5 C6 H6B 111.2 ?
C7 C6 H6B 111.2 ?
H6A C6 H6B 109.1 ?
C6 C7 C8 104.7(2) y
C6 C7 H7A 110.8 ?
C8 C7 H7A 110.8 ?
C6 C7 H7B 110.8 ?
C8 C7 H7B 110.8 ?
H7A C7 H7B 108.9 ?
N1 C8 C7 101.5(2) y
N1 C8 C16 109.2(2) y
C7 C8 C16 110.2(2) y
N1 C8 H8 111.8 ?
C7 C8 H8 111.8 ?
C16 C8 H8 111.8 ?
C11 N10 C3 121.8(2) y
C11 N10 H10 119.1 ?
C3 N10 H10 119.1 ?
O11 C11 N10 125.4(3) y
O11 C11 O12 125.3(3) y
N10 C11 O12 109.3(2) y
C11 O12 C12 120.3(2) y
O12 C12 C13 110.1(3) y
O12 C12 C15 110.3(3) y
C13 C12 C15 113.7(3) y
O12 C12 C14 101.6(2) y
C13 C12 C14 110.3(3) y
C15 C12 C14 110.2(4) y
C12 C13 H13A 109.5 ?
C12 C13 H13B 109.5 ?
H13A C13 H13B 109.5 ?
C12 C13 H13C 109.5 ?
H13A C13 H13C 109.5 ?
H13B C13 H13C 109.5 ?
C12 C14 H14A 109.5 ?
C12 C14 H14B 109.5 ?
H14A C14 H14B 109.5 ?
C12 C14 H14C 109.5 ?
H14A C14 H14C 109.5 ?
H14B C14 H14C 109.5 ?
C12 C15 H15A 109.5 ?
C12 C15 H15B 109.5 ?
H15A C15 H15B 109.5 ?
C12 C15 H15C 109.5 ?
H15A C15 H15C 109.5 ?
H15B C15 H15C 109.5 ?
O16 C16 O17 124.2(2) y
O16 C16 C8 124.2(2) y
O17 C16 C8 111.6(2) y
C16 O17 C17 115.3(2) y
O17 C17 H17A 109.5 ?
O17 C17 H17B 109.5 ?
H17A C17 H17B 109.5 ?
O17 C17 H17C 109.5 ?
H17A C17 H17C 109.5 ?
H17B C17 H17C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C2 1.349(3) y
N1 C8 1.450(3) y
N1 C5 1.467(3) y
C2 O2 1.215(3) y
C2 C3 1.512(4) y
C3 N10 1.442(3) y
C3 C4 1.518(4) y
C3 H3 0.9800 ?
C4 C5 1.519(4) y
C4 H4A 0.9700 ?
C4 H4B 0.9700 ?
C5 C6 1.520(4) y
C5 H5 0.9800 ?
C6 C7 1.524(5) y
C6 H6A 0.9700 ?
C6 H6B 0.9700 ?
C7 C8 1.525(4) y
C7 H7A 0.9700 ?
C7 H7B 0.9700 ?
C8 C16 1.528(4) y
C8 H8 0.9800 ?
N10 C11 1.340(3) y
N10 H10 0.8600 ?
C11 O11 1.208(3) y
C11 O12 1.348(3) y
O12 C12 1.462(4) y
C12 C13 1.508(5) y
C12 C15 1.508(6) y
C12 C14 1.522(4) y
C13 H13A 0.9600 ?
C13 H13B 0.9600 ?
C13 H13C 0.9600 ?
C14 H14A 0.9600 ?
C14 H14B 0.9600 ?
C14 H14C 0.9600 ?
C15 H15A 0.9600 ?
C15 H15B 0.9600 ?
C15 H15C 0.9600 ?
C16 O16 1.191(3) y
C16 O17 1.324(3) y
O17 C17 1.456(3) y
C17 H17A 0.9600 ?
C17 H17B 0.9600 ?
C17 H17C 0.9600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_distance_DA
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N10 H10 0.86 2.33 143.5 3.063(3) O16 2_555 y
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_publ_flag
C8 N1 C2 O2 -26.4(4) y
C5 N1 C2 O2 -172.9(2) y
C8 N1 C2 C3 151.7(2) y
C5 N1 C2 C3 5.2(3) y
O2 C2 C3 N10 29.2(3) y
N1 C2 C3 N10 -148.8(2) y
O2 C2 C3 C4 153.5(2) y
N1 C2 C3 C4 -24.6(2) y
N10 C3 C4 C5 154.5(2) y
C2 C3 C4 C5 33.5(3) y
C2 N1 C5 C4 16.4(3) y
C8 N1 C5 C4 -134.0(2) y
C2 N1 C5 C6 142.3(2) y
C8 N1 C5 C6 -8.0(3) y
C3 C4 C5 N1 -30.5(3) y
C3 C4 C5 C6 -144.1(3) y
N1 C5 C6 C7 27.5(3) y
C4 C5 C6 C7 140.8(3) y
C5 C6 C7 C8 -37.6(3) y
C2 N1 C8 C7 -161.1(2) y
C5 N1 C8 C7 -14.9(3) y
C2 N1 C8 C16 -44.7(3) y
C5 N1 C8 C16 101.5(3) y
C6 C7 C8 N1 31.9(3) y
C6 C7 C8 C16 -83.7(3) y
C2 C3 N10 C11 -106.9(3) y
C4 C3 N10 C11 136.8(3) y
C3 N10 C11 O11 -10.9(5) y
C3 N10 C11 O12 169.7(2) y
O11 C11 O12 C12 3.9(5) y
N10 C11 O12 C12 -176.7(3) y
C11 O12 C12 C13 -66.5(4) y
C11 O12 C12 C15 59.7(4) y
C11 O12 C12 C14 176.5(3) y
N1 C8 C16 O16 -34.8(4) y
C7 C8 C16 O16 75.8(4) y
N1 C8 C16 O17 147.0(2) y
C7 C8 C16 O17 -102.3(3) y
O16 C16 O17 C17 4.2(4) y
C8 C16 O17 C17 -177.7(3) y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9154618
